Think hard before diving in to office romance


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Dear Miss Lonelyhearts: I just met a gorgeous 30-something woman, who now works for the same company I do in a big office. Then I met her again beside my apartment’s indoor pool in a hot-pink bathing suit. Yeow. It had to be fate.

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Dear Miss Lonelyhearts: I just met a gorgeous 30-something woman, who now works for the same company I do in a big office. Then I met her again beside my apartment’s indoor pool in a hot-pink bathing suit. Yeow. It had to be fate.

I couldn’t run away, so we sat down by the pool to chat. I had hoped we wouldn’t hit it off, but we did. Now I’m embarrassed to say I’m down by that pool almost every evening like a hopeful hound waiting for a bone, and she always shows up at some point. We are both trying our best to be “just friends” because of work, but that’s wearing out fast.

The other night I ended up at her door with my hand raised to knock, when I thought, “You idiot! Go home. You have a great job situation you could wreck.” It was a close call. I dragged myself home to my apartment and stayed up all night, wanting her.

Now what? The inevitable is going to happen. I’m hers for the taking if she ever shows up at my door. How do I handle this?

— Damage Control Needed, Downtown

Dear Damage: Sometimes the little fires are already smouldering, and both parties are just waiting for the other to show up with the inevitable gasoline can. Try not to be that one!

Affairs at work can be so much trouble. They rarely stay private. It’s best if you can get into a different part of the business, on a different floor. It’s worth a try right now, before the thing explodes — and it’s highly likely to happen soon from what you both seem to be feeling.


Dear Miss Lonelyhearts: My new boyfriend is great, but he has a physical oddity that kind of freaks me out. He pumps weights to the point that he has a chest that almost looks like a pointed woman’s chest. He mostly wears sweatshirts and sweaters, but everybody knows he is mighty proud of that big chest.

I just don’t know if I can get past this — I don’t like it! Maybe there are things about my body he doesn’t like, but I doubt if he is as petty as I am. I should be ashamed.

He’s otherwise fantastic — kind, handsome and all that. Am I…

— Too Shallow? West End

Dear Shallow: This relationship is a new one, and it should definitely be a short one. Would you want to keep a man in your life who found your chest repellent and had to get past that feeling to be your love partner? Of course not.

Now look at his side of the situation. It’s a shame to waste the body this man spends so much time building on someone who doesn’t like it. You need to get out of the way! If he’s a really nice guy, as you say, he deserves a woman who thinks he’s great.

Regular flat-chested guys will be easy for you to find. Two years of COVID inactivity has seen to that.


Dear Miss Lonelyhearts: I want a better life. I want to marry a woman who loves me. I want to have a nice home and also earn better money. I feel so stupid saying these things out loud, because obviously this is what everyone wants, but I feel so destitute. The economy and inflation make my decent-paying job only able to provide me with a paycheque-to-paycheque existence. With house prices going up every month, I just don’t feel optimistic anymore. How can I start making some of my long-standing dreams of success happen?

— Down and Out at 28, South Winnipeg

Dear Down and Out: There are ways up and out but they now look different to the old means of climbing the ladder in a company. People who are breaking out of depressing modes of thinking in the 2020s are exploring “side gigs” (side businesses or part-time jobs), while hanging onto their regular bill-paying jobs. But here’s the hot clue so many people are missing: You have to search your heart. It can’t be any old side-gig. In order to have extra personal energy and a feeling of renewed enjoyment in life, you need a side business that expresses your real interests — perhaps hidden ones.

Your big mistake? Being angry at your regular job, which can cause depression, inactivity and “failure to launch.” That precious regular job enables you to follow other dreams. Stop singing the blues and look at the money from that primary job as fuel for the side-gigs — vehicles which perhaps could bring big, meaningful success.

Some day in the future, you may look back and say, “I only made it with my new business because my old business only paid the rent, and I was forced to take my other skills and interests seriously.”

Please send your questions and comments to or Miss Lonelyhearts c/o the Winnipeg Free Press, 1355 Mountain Ave., Winnipeg, MB, R2X 3B6.

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